Hydrochloric Acid → HCID 178463378, compound

HRID 241180Notes

Reaction equation

[ClH:1].O1CCOCC1.[CH2:8]([NH:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([C:20]3[CH:21]=[CH:22][C:23]4[O:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C:24]=4[CH:37]=3)[CH:18]=[CH:19][C:13]=2[N:12]=1)[CH3:9]>CO>[ClH:1].[ClH:1].[CH2:8]([NH:10][C:11]1[NH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]4[O:29][CH2:28][CH2:27][NH:26][CH2:25][C:24]=4[CH:37]=3)=[CH:16][C:14]=2[N:15]=1)[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of hydrogen chloride in dioxane (4 M, 2.09 mL, 8.3 mmol) was added to 1,1-dimethylethyl 7-[2-(ethylamino)-1H-benzimidazol-6-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (337 mg, 0.83 mmol) in methanol (4 mL). The mixture was heated to 60° C. and stirred for 1 h before cooling to rt. The volatile materials were removed to provide N-ethyl-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-benzimidazol-2-amine dihydrochloride in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ 12.85 (d, 2H), 9.48 (br s, 2H), 9.11-9.03 (m, 1H), 7.77 (d, 1H), 7.63 (dd, 1H), 7.55 (d, 1H), 7.52-7.42 (m, 2H), 7.19 (d, 1H), 4.42 (br s, 2H), 4.28-4.20 (m, 2H), 3.55-3.41 (m, 4H), 1.26 (t, 3H); MS (EI) for C18H20N4O: 309 (MH+).

Workup

temperaturebefore cooling to rt
customThe volatile materials were removed

Sources & evidence

ORD record: ord-7a9903d974c8482ba47cf92ba6ab9683
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

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